Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of 6-(trifluoromethyl) isoquinoline-5-ol

A technology of trifluoromethyl isoquinoline and trifluoromethyl, which is applied in the field of synthesis of 6-(trifluoromethyl) isoquinoline-5-ol, can solve problems such as incapability of large-scale production, and achieve easy The effect of amplification, reasonable process selection and low cost of raw materials

Active Publication Date: 2020-12-18
SUZHOU KANGRUN PHARMA
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At this stage, there is no published synthetic route of 6-(trifluoromethyl)isoquinolin-5-ol. At present, the main synthetic method of 6-trifluoromethylisoquinoline is to pass p-benzylamine under microwave Condensation reaction and sulfuric acid ring closure reaction to generate 6-(trifluoromethyl)isoquinolin-3-ol. In the existing synthetic route of 6-trifluoromethylisoquinoline, the condensation reaction needs to be carried out under microwave conditions. cannot be mass produced

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of 6-(trifluoromethyl) isoquinoline-5-ol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0041] The present invention will be further described below in conjunction with specific examples, but the examples are only exemplary and do not constitute any limitation to the scope of the present invention. Those skilled in the art should understand that the details and forms of the technical solutions of the present invention can be modified or replaced without departing from the spirit and scope of the present invention, but these modifications and replacements all fall within the protection scope of the present invention.

[0042] The synthesis process of 6-(trifluoromethyl)isoquinolin-5-amine of the present invention is based on the raw material of m-trifluoromethylphenethylamine, and undergoes amino protection, ring closure, hydrolysis, bromination and debromination of alkenes with TFAA. and dehydroaromatization to obtain 7-trifluoromethylisoquinoline, and NBS for 5-bromination to generate 5-bromo-7-trifluoromethylisoquinoline, methoxylation and demethylation with sodiu...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthesis method of 6- (trifluoromethyl) isoquinoline-5-ol, which comprises the following steps of by using p-trifluoromethyl phenylethylamine as a raw material, carrying outamino protection, cyclization, hydrolysis, bromination, debromination alkene insertion and dehydroaromatization on the p-trifluoromethyl phenylethylamine and TFAA to obtain 7-trifluoromethyl isoquinoline, and carrying out 5-site bromination on the 7-trifluoromethyl isoquinoline and NBS to generate 5-bromine- 7-trifluoromethyl isoquinoline, and carrying out methoxylation and demethylation with sodium methoxide to obtain 6-(trifluoromethyl) isoquinoline-5-alcohol. The method is simple in synthetic route, reasonable in process selection, low in raw material cost, simple and easily available in raw materials, convenient to operate and post-treat, high in total yield, free of highly toxic reagents and easy to amplify, and can be used for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and in particular relates to a synthesis method of 6-(trifluoromethyl)isoquinolin-5-ol. Background technique [0002] 6-(Trifluoromethyl)isoquinolin-5-ol is a key pharmaceutical intermediate, and its 6-position trifluoromethyl group has excellent characteristics as a fluorine-containing substituent group. It can effectively improve bioavailability and improve pharmacokinetic properties. The 6-trifluoromethylisoquinoline structure is often used as a modification group to improve the properties of drug candidate molecules. The hydroxyl group at the 5-position can be well connected with various compounds through esterification or amidation, thereby expanding its applicability. Acharya R A et al. developed a novel aminoisoxazoline compound (WO2017069980 A1) as an α7-nicotinyl acetylcholine receptor agonist, which can improve cognitive impairment diseases such as Al...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D217/02
CPCC07D217/02
Inventor 晋浩文徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com